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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 19:27:45 UTC

Update Date

2022-09-22 18:35:04 UTC

HMDB ID

HMDB0341167

Secondary Accession Numbers

None

Metabolite Identification

Common Name

isomaltulose

Description

isomaltulose belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. isomaltulose is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on isomaltulose.

Structure

MOL SDF PDB SMILES InChI

  Mrv1652310282001082D          

 23 24  0  0  1  0            999 V2000
   -6.4088   -2.2303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9239   -1.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1034   -1.6491    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6184   -0.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7980   -1.0679    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3130   -0.4005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6486    0.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1637    1.0206    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4186    1.8053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512    2.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3032    2.9033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1991    2.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4541    3.6879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0837    1.8053    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2991    2.0602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3387    1.0206    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8538    0.3532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4624   -1.8216    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6419   -1.9078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9473   -2.4890    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6118   -3.2427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7678   -2.4028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2527   -3.0702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  6  0  0  0
  5 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0341167

> <DATABASE_NAME>
hmdb

> <SMILES>
OC[C@H]1O[C@H](OC[C@H]2OC(O)(CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C12H22O11/c13-1-4-6(15)8(17)9(18)11(22-4)21-2-5-7(16)10(19)12(20,3-14)23-5/h4-11,13-20H,1-3H2/t4-,5-,6-,7-,8+,9-,10+,11+,12?/m1/s1

> <INCHI_KEY>
PVXPPJIGRGXGCY-TZLCEDOOSA-N

> <FORMULA>
C12H22O11

> <MOLECULAR_WEIGHT>
342.297

> <EXACT_MASS>
342.116211528

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
30.970997907005405

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{[(2R,3S,4S)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy}oxane-3,4,5-triol

> <ALOGPS_LOGP>
-3.23

> <JCHEM_LOGP>
-4.528834963666666

> <ALOGPS_LOGS>
0.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.101606988230476

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.279238125855457

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083422322407

> <JCHEM_POLAR_SURFACE_AREA>
189.52999999999997

> <JCHEM_REFRACTIVITY>
68.77409999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.86e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
palatinose

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-OCT-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-OCT-20         0                                  
HETATM    1  O   UNK     0     -11.963  -4.163   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0     -11.058  -2.917   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.526  -3.078   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -8.621  -1.832   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -7.090  -1.993   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -6.184  -0.748   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -6.811   0.659   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.906   1.905   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -6.381   3.370   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -5.136   4.275   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -6.166   5.419   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.105   5.419   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.581   6.884   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.890   3.370   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.425   3.846   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -4.366   1.905   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.460   0.659   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -6.463  -3.400   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.932  -3.561   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -7.368  -4.646   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.742  -6.053   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -8.900  -4.485   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -9.805  -5.731   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   14                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12                                                            
CONECT   14   10   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    8   17                                                  
CONECT   17   16                                                            
CONECT   18    5   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    3   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-O-alpha-D-Glucopyranosyl-D-fructose	ChEBI
6-O-alpha-D-Glucopyranosyl-D-fructofuranose	Kegg
6-O-a-D-Glucopyranosyl-D-fructose	Generator
6-O-Α-D-glucopyranosyl-D-fructose	Generator
6-O-a-D-Glucopyranosyl-D-fructofuranose	Generator
6-O-Α-D-glucopyranosyl-D-fructofuranose	Generator
D-Fructose, 6-O-alpha-D-glucopyranosyl-, monohydrate	HMDB
Isomaltulose anhydrous	HMDB
6-O alpha-D-Glucopyranosyl-D-fructose	HMDB
Isomaltulose monohydrate	HMDB
Isomaltulose	ChEBI

Chemical Formula

C₁₂H₂₂O₁₁

Average Molecular Weight

342.297

Monoisotopic Molecular Weight

342.116211528

IUPAC Name

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{[(2R,3S,4S)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy}oxane-3,4,5-triol

Traditional Name

palatinose

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@H](OC[C@H]2OC(O)(CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C12H22O11/c13-1-4-6(15)8(17)9(18)11(22-4)21-2-5-7(16)10(19)12(20,3-14)23-5/h4-11,13-20H,1-3H2/t4-,5-,6-,7-,8+,9-,10+,11+,12?/m1/s1

InChI Key

PVXPPJIGRGXGCY-TZLCEDOOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

O-glycosyl compound
Disaccharide
C-glycosyl compound
Oxane
Tetrahydrofuran
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

glycosylfructose (CHEBI:18394 )
Disaccharides (C01742 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-3.2	ALOGPS
logP	-4.5	ChemAxon
logS	0.3	ALOGPS
pKa (Strongest Acidic)	10.28	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	189.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	68.77 m³·mol⁻¹	ChemAxon
Polarizability	30.97 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - isomaltulose GC-MS (TMS_3_29) - 70eV, Positive	Not Available	2022-08-08	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - isomaltulose 10V, Positive-QTOF	Not Available	2022-08-10	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - isomaltulose 20V, Positive-QTOF	Not Available	2022-08-10	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - isomaltulose 40V, Positive-QTOF	Not Available	2022-08-10	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - isomaltulose 10V, Negative-QTOF	Not Available	2022-08-10	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - isomaltulose 20V, Negative-QTOF	Not Available	2022-08-10	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - isomaltulose 40V, Negative-QTOF	Not Available	2022-08-10	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Isomaltulose

METLIN ID

Not Available

PubChem Compound

439559

PDB ID

Not Available

ChEBI ID

18394

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Neto FC, Raftery D: Expanding Urinary Metabolite Annotation through Integrated Mass Spectral Similarity Networking. Anal Chem. 2021 Sep 7;93(35):12001-12010. doi: 10.1021/acs.analchem.1c02041. Epub 2021 Aug 26. [PubMed:34436864 ]

Showing metabocard for isomaltulose (HMDB0341167)

MOL for HMDB0341167 (isomaltulose)

3D MOL for HMDB0341167 (isomaltulose)

3D SDF for HMDB0341167 (isomaltulose)

3D-SDF for HMDB0341167 (isomaltulose)

PDB for HMDB0341167 (isomaltulose)

3D PDB for HMDB0341167 (isomaltulose)

SMILES for HMDB0341167 (isomaltulose)

INCHI for HMDB0341167 (isomaltulose)

Structure for HMDB0341167 (isomaltulose)

3D Structure for HMDB0341167 (isomaltulose)

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra

NMR Spectra